Phthalocyanine compound, preparation method and application as single/two-photon fluorescent probe in cancer targeting and mitochondria labeling

A compound and phthalocyanine technology, applied in the field of phthalocyanine-based compounds and their preparation, can solve the problems of non-phototoxicity, limited application of phthalocyanine, and destructiveness of biological tissues of research objects, and achieves good affinity, large absorption cross-section, and good application. effect of value

Active Publication Date: 2015-08-26
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, phthalocyanine will be accompanied by the generation of singlet oxygen in the process of fluorescence emission, which is extremely destructive to the research object, especially biological tissues, and is not conducive to the continuation of the study of biological processes
This feature greatly limits the application of phthalocyanine as a red-near-infrared fluorescent probe
Therefore, so far, no phototoxic phthalocyanine-based fluorescent probes have been reported, and no phototoxic phthalocyanine-based fluorescent probes capable of simultaneous single- and two-photon mitochondrial imaging have been reported.

Method used

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  • Phthalocyanine compound, preparation method and application as single/two-photon fluorescent probe in cancer targeting and mitochondria labeling
  • Phthalocyanine compound, preparation method and application as single/two-photon fluorescent probe in cancer targeting and mitochondria labeling
  • Phthalocyanine compound, preparation method and application as single/two-photon fluorescent probe in cancer targeting and mitochondria labeling

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] The preparation of the phthalocyanine base compound shown in embodiment 1, formula (II)

[0061] (1) Preparation of ethyl 4-[3,4-dicyanophenoxy]butanoate (a)

[0062]

[0063] Weigh 0.55g (3.8mmol) 4-hydroxyphthalonitrile and 1.3g (6.9mmol) ethyl 4-bromo-n-butyrate, and 1.6g K 2 CO 3 Dissolve in DMF (10mL), stir at room temperature for 24h, then drain the DMF under reduced pressure, dissolve the residue in chloroform and wash with water three times, collect the organic layer and remove the organic solvent chloroform under reduced pressure, the crude product is separated by silica gel column chromatography to obtain White solid, yield 83.6%.

[0064] 1 H NMR (300MHz, CDCl 3 , 25℃, TMS): δ=7.72-7.70(d, J=8.7Hz, 1H, ArH), 7.27-7.17(m, 2H, ArH), 4.20-4.10(m, 4H, CH 2 ), 2.52(t, J=7.2Hz, 2H, CH 2 ),2.20-2.12(m,2H,CH 2 ), 1.27(t, J=7.2Hz, 3H, CH 3 );

[0065] (2) Preparation of three [(4-tert-butyl)phenoxy]-one[(4-n-butyrate)phenoxy]zinc phthalocyanine (c)

[006...

Embodiment 2

[0077] Embodiment 2, center ion is Ni 2+ Preparation of phthalocyanine-based compounds

[0078] The detailed steps are the same as in Example 1, except that the metal salt is changed to nickel acetate in the step (2).

Embodiment 3

[0079] Embodiment 3, center ion is Mg 2+ Preparation of phthalocyanine-based compounds

[0080] The detailed steps are the same as in Example 1, except that the metal salt is changed to magnesium chloride in the step (2).

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Abstract

The invention relates to a phthalocyanine compound, a preparation method and an application as a single / two-photon fluorescent probe in cancer targeting and mitochondria labeling. The phthalocyanine compound has a structure of formula (I) and is an asymmetric phthalocyanine metal complex; R represents a polypeptide containing an RGD sequence, n is 0-6; the phthalocyanine compound not only has unique selectivity for cancer cells, but also can realize specific localization in live cell mitochondria, and is a multifunctional fluorescent probe. The invention also provides the preparation method of the phthalocyanine compound, wherein the preparation method is simple in process and wide in application range. The phthalocyanine compound overcomes the common phototoxicity of phthalocyanine; under 12 J / cm<2> of red light irradiation energy, the survival rate of cells is above 95%; and the phthalocyanine compound has good application value in two-photon tumor imaging and mitochondria imaging.

Description

technical field [0001] The invention relates to a phthalocyanine-based compound and a preparation method thereof. The phthalocyanine-based compound can be used for cancer-targeted fluorescence imaging and living cell mitochondrial fluorescence imaging, can be used as a single-photon or two-photon fluorescent probe, and belongs to the field of organic functional materials. Background technique [0002] A major challenge in current cancer treatment is how to effectively distinguish tumors from healthy tissues. Since cancer cells are necessarily different from normal cells, cancer diagnosis and treatment methods are mainly based on these differences. The unique receptors on the surface of cancer cells have always attracted the interest of researchers as markers of tumor cells. Using a ligand with a specific affinity for the receptor as a targeting molecule, and cross-linking with a imaging agent or an anticancer drug, can effectively achieve the accumulation of drugs in tumors...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/12C09K11/06C12Q1/02
Inventor 刘伟刘久荣栾立强方文娟
Owner SHANDONG UNIV
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